| Título |
Chemoenzymatic synthesis of carbasugars from iodobenzene |
| Autores |
Boyd, DR , Sharma, ND , MOREJÓN LLAMAS, NOEMÍ, Malone, JF , O'Dowd, CR , Allen, CCR |
| Publicación externa |
Si |
| Medio |
ORGANIC & BIOMOLECULAR CHEMISTRY |
| Alcance |
Article |
| Naturaleza |
Científica |
| Cuartil JCR |
2 |
| Cuartil SJR |
1 |
| Impacto JCR |
2.547 |
| Impacto SJR |
1.293 |
| Fecha de publicacion |
01/01/2005 |
| ISI |
000229067300020 |
| DOI |
10.1039/b502009c |
| Abstract |
The versatile enantiopure cis-dihydrodiol metabolite 1, formed by bacterial metabolism of iodobenzene, has been used for the synthesis of the pyranose carbasugars (pseudosugars) carba-β-D-altropyranose 2, carba-α-L-galactopyranose 3, carba-β-D-idopyranose 4 and carba-β-L-glucopyranose 5. Substitution of the iodine atom by a carbomethoxy group, stereoselective catalytic hydrogenation of an α,β-unsaturated ester, and regioselective inversion of one or two allylic chiral centres are the key steps used in the synthesis of carbasugars 2-5. The relative and absolute configurations of compounds 2-5 were established by a combination of stereochemical correlation, X-ray crystallography and H-1-NMR spectroscopy. |
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